Becoming a supervisor is one of the transitional phases that occur at workplaces, unfolding as either individual or situational opportunities or challenges or combination thereof. The literature reveals that upon appointment into supervisory positions, most first-time supervisors are summarily presumed ready to assume their responsibilities as seasoned supervisors often performing their supervisory roles without proper preparation. This study asserts that providing support measures for reflective practice is invaluable as it enables the effective transition of first-time supervisors into their new role. This study followed a two-pronged process in assessing and exploring the transitional experiences of self-defined first-time supervisors within a social service organisation, with different types of triangulation applied in the process, namely methodological, theoretical and data triangulation. Both pragmatist and constructivist paradigms were used, thus dispelling the perceived incompatibility of the different paradigms. A mixed methods inquiry was undertaken to elicit for richer data on supervision transition, which would not be possible if each approach was applied individually. The theoretical triangulation involving both the Experiential Learning Theory and Schlossberg's Transition Theory provided the underlying theoretical basis for the phenomenon in focus. In this case, data were collected sequentially from questionnaires (n=40) and semi-structured interviews (n=13), which yielded descriptive and thematic insights, respectively. Precisely, as first-time supervisors transition into the supervisory role, they are confronted with diverse needs, challenges and responsibilities. Supervision relationships and the interface between organisational and professional contexts determine the nature and extent of transition. The study recommends the development of an integrated supervision strategy that embraces managerial synergies and professional supervision responsibilities and the need for devising reflective capacity-building measures to address the ongoing supervision needs. The study further recommends the development of an organisation that considers the development of organisation- specific supervision policy necessary to guide the supervision practice in general and supervision transition in particular. Lastly, as far as the future studies are concerned, it is recommended that undertaking a countrywide study could provide insight into the transitional experiences in the sector as a whole. An evaluative study is capable of providing criteria for measuring effective supervisory transition.